1.14.19.9: tryptophan 7-halogenase

This is an abbreviated version!
For detailed information about tryptophan 7-halogenase, go to the full flat file.

Reaction

Synonyms

EC 1.14.14.7, FAD-dependent halogenase, flavin-dependent halogenase, flavin-dependent tryptophan halogenase, halogenase, KtzQ, L-tryptophan-7-halogenase, PrnA, RebH, Trp 7-hal, Trp halogenase, Trp-7-Hal, Trp-7-halogenase

ECTree

     1 Oxidoreductases

         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen

             1.14.19 With oxidation of a pair of donors resulting in the reduction of O₂ to two molecules of water

                1.14.19.9 tryptophan 7-halogenase

Advanced search results

Do not include text mining results

Include results (more...)

Include results (more...)

Results	in table
578	AA Sequence
1	CAS Registry Number
10	Cloned(Commentary)
15	Cofactor
5	Crystallization (Commentary)
3	General Information
1	Inhibitors
9	KM Value [mM]
3	Molecular Weight [Da]
17	Natural Substrates/ Products (Substrates)
23	Organism
5	Pathway
9	PDB ID
4	pH Optimum
10	Protein Variants
8	Purification (Commentary)
8	Reaction
7	Reaction Type
23	Reference
3	Specific Activity [micromol/min/mg]
46	Substrates and Products (Substrate)
2	Subunits
32	Synonyms
1	Systematic Name
4	Temperature Optimum [°C]
11	Turnover Number [1/s]

Reaction

print visible entries

print all entries

Go back to the abbreviated version
of the Enzyme Summary Page.

Reaction on EC 1.14.19.9 - tryptophan 7-halogenase

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.

top print hide show all columns Go to Reaction Search

Please wait a moment until the data is sorted. This message will disappear when the data is sorted.

REACTION

REACTION DIAGRAM

COMMENTARY

ORGANISM

UNIPROT

LITERATURE

tryptophan + FADH2 + chloride + O2 + H+ = 7-chloro-L-tryptophan + FAD + 2 H2O

8 entries

tryptophan + FADH2 + chloride + O2 + H+ = 7-chloro-L-tryptophan + FAD + 2 H2O

reaction mechanism

Lentzea aerocolonigenes

-

685105

tryptophan + FADH2 + chloride + O2 + H+ = 7-chloro-L-tryptophan + FAD + 2 H2O

FADH2 and O2 form an 4alpha-FAD-OOH intermediate that decays to 4alpha-FAD-OH. Tryptophan likely does not react directly with any flavin intermediate. Substrate chlorination occurs after completion of the flavin redox reactions

Lentzea aerocolonigenes

-

672189

tryptophan + FADH2 + chloride + O2 + H+ = 7-chloro-L-tryptophan + FAD + 2 H2O

FADH2 reacts with O2 to make peroxyflavin, which is decomposed by Cl-. the resulting HOCl is guided through the tunnel to tryptophan, where it is activated to participate in electrophilic aromatic substitution

Pseudomonas fluorescens

-

677119

tryptophan + FADH2 + chloride + O2 + H+ = 7-chloro-L-tryptophan + FAD + 2 H2O

monooxygenase-like mechanism proposed. First, FADH2 is produced by a flavin reductase using NADH. FADH2 binds to flavin-free enzyme and reacts to enzyme-bound 4alpha-flavin hydroperoxide which attacks L-tryptophan. Activated tryptophan is attacked by chloride as a nucleophile, the resulting halohydrin is dehydrated to the end product 7-chlorotryptophan

Pseudomonas fluorescens

-

671187

tryptophan + FADH2 + chloride + O2 + H+ = 7-chloro-L-tryptophan + FAD + 2 H2O

proposed mechanism: after formation of a FAD-OOH intermediate, the reactive chlorine is generated as a FAD-O-Cl intermediate. Chlorination of L-tryptophan proceeds by attack of the aromatic pi electrons on the intermediate in a two-electron mechanism and abstraction of a proton generates the final product

Lentzea aerocolonigenes

Q8KHZ8

676785

tryptophan + FADH2 + chloride + O2 + H+ = 7-chloro-L-tryptophan + FAD + 2 H2O

reaction mechanism, combined quantum mechanical/molecular mechanical (QM/MM) calculations of potential energy and free energy surfaces, using the structure, PDB ID 2AR8, and employing density functional theory. First reaction step is the formation of an arenium ion (Wheland intermediate), the second reaction step is the deprotonation of the Wheland intermediate by residue E346 oxygen, at the final stage of the mechanism residues K79 and E346 are regenerated

Pseudomonas fluorescens

P95480

746470

tryptophan + FADH2 + chloride + O2 + H+ = 7-chloro-L-tryptophan + FAD + 2 H2O

proposed mechanism: after formation of a FAD-OOH intermediate, the reactive chlorine is generated as a FAD-O-Cl intermediate. Chlorination of L-tryptophan proceeds by attack of the aromatic pi electrons on the intermediate in a two-electron mechanism and abstraction of a proton generates the final product

Lentzea aerocolonigenes 39243

-

-

tryptophan + FADH2 + chloride + O2 + H+ = 7-chloro-L-tryptophan + FAD + 2 H2O

-

-

-

-